When Roads Diverge
by IndigoCaelum
Summary: Ten years ago, Sam up and left for Stanford. Ten years ago, John hit a lead and went to hunt down Mary's killer. Ten years ago, Dean was left in the dust, on his own for the first time in his life. Where are they at now?
1. Chapter 1

Disclaimer: Sadly, I hold no rights to Supernatural, nor its characters.

A/N: Though I've been reading fanfiction for quite some time now, this is my first story. Please read and review, advice is always welcome. Enjoy.

When Roads Diverge

10 Years Ago

It didn't take long for Sam to realize that he didn't have what you would consider a "normal" family.

He understood that most kids had a permanent home.

Not a motel room that held the must of previous occupants, or a car with a grumbling thunder that could put you to sleep in minutes.

He understood that most kids had a mom who gently woke them in the morning; a mom who made a nice breakfast before sending them off to school.

Not a brother on the cusp of adulthood. Not a brother who raided the cabinets for a box of Lucky Charms and a cup of milk. That is, if there was any left.

Did he need to spend a night out at the pool hall? Or a poker game?

He understood that most kids had a dad who worked from nine to five. One that left around dawn, but returned before dusk.

Not a father who left with a note on the counter, twenty dollars alongside, that read: "Gone on business. Back in a few days," with a phone number scrawled beneath. But most importantly, Sam always knew that having a family that hunted the supernatural, the things that go bump in the night, the things of nightmares, was not what most would call "normal".

Especially when they came home bloody and battered.

They'd stumble in before any rooster would dare crow. The moon wasn't ready to say farewell; the sun wasn't ready to face the day.

With bumps that would soon mottle with the coloring of dark bruising, and cuts that were too deep for a band-aid.

Sam understood this wasn't normal. The training, the moving, the hunting, the illegalities.

Unlike Dad and Dean, he was cut out for things beyond silver bullets and holy water.

As much as Sam appreciated and loved Dean for all he'd done for him, he didn't want to become him. Eating the diner special morning, noon, and night and hooking up with wayward women in roadside bars wasn't he'd been planning for.

What he had been planning on was deep within his duffle. With the papers hidden like a needle in a haystack, was his admissions package and guidelines for Stanford.

 _Stanford._

He understood that with an opportunity like this, for someone like _him_ , and he couldn't deny himself. It was every hope and dream wrapped up into one. After all of the portfolios and testing, and he had finally done it. He was going to college; going to earn a degree; going to live Dean's idea of an 'apple pie life'. Not living a life with Feds on your six or stitching up knife wounds in rusted out shacks.

He understood that this, right here, right now, was happening. With or without his family, Sam was leaving the family business.

* * *

"Simple salt and burn, Sam. Nothing more, nothing less," John muttered.

He sat on the worn bed, the mattress dipping beneath his large stature. Bent over, he laced his boots up quickly, efficiently knotting them only the way a man of the military could. The precision he applied to tying shoes was equivalent to any factor that could effect the result of a hunt. Every piece mattered in the puzzle.

The tension in the room was palpable. A string drawn taught, waiting for the inevitable 'snip' that would break it in two.

It seemed to be a regular occurrence these days.

If John wasn't stepping on Sam's heels, then Sam was breathing down the back of John's neck.

Tonight was a combination of both.

John's eyes whipped up to meet Sam's.

Hard as granite, he held his gaze.

"I said move out. That's an order Sam," John barked, what little patience having quickly evaporated. Rocking slightly onto the balls of his feet, he rose to his full height.

"Sir, yes sir," Sam muttered sarcastically. His gangling form rose, grabbing his packed bags and marched out the door. The tension could be felt thinning with every step he took out the door, away from John.

John moved across the room, his callused hands tightly grasping the handle of his faded duffle. It showed its age well, having been through more adventures than the usual bag called for. Being dragged from hunt to hunt was more than most bags went through. The deep stretch marks and faint tears were worn with pride from each victory, no matter how small.

The past couple of months had shortened John's temper, the needle on the gage pushing past the 'WARNING' level, heading towards 'EXPLOSIVE'.

After years of research, John was finally making headway in the hunt for Mary's killer. And nothing was going to stop him from achieving the goal he had set all those years ago. He was going to end it once and for all. Maybe not today, but soon.

But his patience had already ran as thin as the shitty rest stop toilet paper.

With two grown boys along for the ride, frustrations ran high.

Sam, as any typical teenager, spent his time constantly testing John's limits. Whether they were picking the diner for dinner, or having to move towns for a new hunt (therefore the school, too), everything set the other off.

As for Dean, he was the constant barrier that kept the needle from pushing over into 'EXPLOSIVE'. Always doing his best to follow in his father's footsteps, John's irritation was building towards Dean as well. He turned around, and Dean was there. He woke up, and Dean was first to start conversation, keeping a line of questions coming, even before coffee had been dispensed. At twenty-one years old, John was beginning to realize Dean had no plans of leaving without a shove. A hard one at that.

Emotions were high, and everyone needed a break.

But there was nothing about breaks in John Winchester's book, not until the breaking point was hit.

* * *

Shoving the key into the lock and turning, Dean pushed his way through the motel room door. It'd been a painstakingly long drive back to the motel from Louisville.

The hunt itself was fairly simple, and hadn't required much time. He'd been damn surprised when John said he could fly solo. It was a rarity for Dean to hunt alone, and he sure as hell would take any chance to prove his skills as a hunter to his father. Any sort of approval from John was like winning an Olympic medal, something to be down right proud of.

The only downfall was leaving Sam and John along together. You might as well be locking God and Lucifer in a cage together. They were like oil and water, always in disagreement, never blending together. Though Dean hated being in the middle- God, how he hated it- it was where he placed himself. For the safety of both Sam and Dad.

Sam was a great kid, in all the right kind of ways, he just saw their lives in a different perspective than himself and John. Sam didn't want to be one of 'Dad's soldiers' like pointed Dean out as. The hero-worship he received from Sam was quickly dwindling down to it's last thread. He wasn't the cool big brother who got the chicks and drove that metal beast of a car. He was now delegated to the brother who was a dropout, fishing around for witty remarks and some spectacular nothing in an empty pond.

What was forgotten was that he was the brother who had given his life for those around him instead. He was the one who took up the role of father in Sam's case, helping him finish science projects and packing his lunch. He was the one who made sure John made it into bed when he had too much of a good time with Jack and Jim. But as long as Sam was safe, his dad, too, he was alright with that. If they were happy, he'd damn well try to be, too.

With blood shot eyes and shaky hands, Dean assessed the bleak motel room. To his confusion, he tossed his duffle onto the nearest bed and turned about.

Instead of an assortment of John and Sam's belongings scattered around, the room was practically empty. Though there were empty plastic coffee cups, and leftover pizza boxes, not a single personal belonging was in the room.

With a sinking feeling in his gut, Dean crossed the room with heavy steps to the small desk. Only one thing had been left behind.

The white notebook paper contrasted harshly with the cheaply stained wood. On the single sheet of paper, was a letter:

 _Dean,_

 _Sam's gone- left for Stanford. Don't try and contact him._

 _I've picked up a trail of information relating to your mother; I'll be gone for a while._

 _There's a case up in North Dakota to check out._

 _Motel room is payed for the next two days._

 _Be safe._

 _Dad_

With green eyes made vibrant by the gloss of unshed tears, Dean rocked back and forth on his heels, absorbing the few words left for him. As the rivulets of tears rolled down his face, and the small cracks engraved themselves into his heart, he understood.

He understood things were no longer going to be "normal".


	2. Chapter 2

**Disclaimer: I hold no ownership to Supernatural, I just like playing in the sandbox.**

7 Years Ago

 _Palo Alto, California_

The sun set an array of colors through the worn windows of the apartment as early evening rolled around. The beauty of this weather was the lack of need for electricity. A couple less dollars Sam would have to pay on the electric bill at least.

Another year of school rolled to an end; an arrangement of perfect exam scores left his junior year on a good note.

Life at Stanford for the past three years could only be described as perfection. To Sam's satisfaction, he'd done everything he could have possibly dreamed of accomplishing at college.

He was receiving an extraordinary education from some of the finest professors in their field. No longer did he have to constantly make sure his transcripts were delivered successfully to each new school. He didn't have to jump into school on a different topic than the last every month or two and catch up on a dime.

For the first time, Sam was able to forge relationships with people who didn't know how to correctly put salt lines by the windows, or the correct pronunciations for the Latin found in an exorcism ritual. They were your average, run of the mill college students- besides the fact they were all relatively smart, given their admission to Stanford. But Sam found he had a group of friends who he could keep for more than a month, friends who actually knew that he preferred a salad over a greasy burger, and that he really didn't like to talk about his life before Stanford.

The one person who was able to push those limits without a glare and change of conversation was Jess.

Jessica Moore.

Sam's escape from the world of the supernatural had granted him the ability to find Jess. Laid-back and kind to a fault, he'd fallen head over heels for the curly-haired woman. After being introduced at a house part at his friend Bill's place, the two sat for hours, chatting about everything from favorite foods to their biggest pet peeves.

Whether it was love at first site or not, it didn't change the fact that Jess made him in inexplicably happy. After dating for about six months, they had decided there was no better time to move into together than the present. Looking about the apartment filled with a combination of his and Jessica's belongings, some that were both of theirs, Sam felt a lump in his throat begin to knot.

He was home.

It wasn't the amount of items in the building, or the fact that he'd lived there longer than he had any motel that made it home.

It was the fact that at the end of the day, when classes were done and he returned to the apartment, and he sat down, that he could feel himself not only relax into the worn love seat, but the very essence of the apartment. His senses would relax, acknowledging the warm hug that he received in exchange. His heart felt at ease here, and that was what really mattered.

Sam broke from his thoughts as he heard the lock on the door jiggle and the handle turn. Seconds later, Jess appeared around the corner. A messenger bag hanging across her slim figure, full curly blonde hair falling about her shoulders. Though she groaned in irritation with the ringlets, claiming them frizzy and uncontrollable, Sam loved the golden halo of curls that framed her face.

Pulling the bag from her body, she hung it on a nearby hook. Pausing to give Sam a kiss of greeting, she headed towards the kitchen.

Sounds of rummaging could be heard from Sam's seat on the couch. "We need to make a run for groceries, or the only thing we'll be eating is cardboard from all these empty boxes," Jess yelled.

With a groan, Sam grumbled, "Isn't there anything left we can eat? What about take-out? That could hold us over 'til tomorrow."

His attention snapped to the kitchen doorway to a small hand stuck around the corner, rattling a box of mac-n-cheese. As quickly as the smile had appeared, the easy going smile dropped from Sam's face. Replacing it was a sickly pallor and frown. Popping her head back around the corner, Jess took in the sudden change in Sam's expression. With a frown, she quickly said, "You know, takeout sounds pretty good. I'll run down the street and pick up some Chinese." Grabbing some cash off of the counter, she crossed back over to Sam, giving him a peck on the cheek and heading out the door.

Sam tried _really_ hard not to think about his life prior to Stanford.

 _Really hard_.

After the whole "College v. Hunting" debacle with his dad, Sam had worked so hard to leave the 'family business' and his family behind. But on certain occasions, the part of his brain that he had closed those memories off to opened up and left a gaping hole with memories leaking out.

Some bad, some good.

The good memories usually pertaining to times with Dean. One in particular, being his ability to make fifty different versions of macaroni and cheese, when it was the only thing you had left to eat or could afford. Even if all of the different versions were weird concoctions that would set most rocking on their heels, gagging on the strange variety.

As bad as life on the hunt had been, Dean had always been there to lessen the pain.

Dean had made long, boring road trips into a day full of 'I spy' and '20 Questions'.

Dean had made getting stitches seem like no big deal, just a scrape.

Dean had made a shitty motel room into a small home with his own persona.

But Dean had made it seem like being a soldier to John was mandatory..

If John said " _jump!_ ", you jumped.

If John said " _roll over!_ ", you rolled over.

If you didn't, you would be sorry.

And getting out of the family business? You'd be shit out of luck to convince John.

All Sam had wanted to do was to be normal. In doing so, it meant tearing his family apart.

As much as Sam loved Dean, for once in his life he had wanted to do something for himself. And if Dean wasn't willing to step outside of John's shadow, what was the point in sticking around? If he hadn't left then, he would have never gotten out.

He would have lived a life with shadows always lurking behind him.

A life with too many horrors.

As Jess walked in the door, hands grasping bags full of Chinese takeout, the last hour of sunlight gleaming behind her, Sam knew walking away from his family had created a new one in Jessica and his friends. A family that wasn't ruled like a dictatorship rather than a democracy.

He was living the 'American Dream'; an apple pie life as Dean would say.

And that was better than perfect to him.

* * *

 **A/N**

 **Sorry for the wait and thank you for your patience! I've had a very busy Christmas break, with no time to sit down and write. Hopefully more to come soon, please read and review. Hope this satisfies your appetite for now!**


	3. Chapter 3

3 Years Ago

 _Upper Peninsula, Michigan_

As he shifted the truck into park, John laid his head back against the cushioned headrest of the truck, his head sinking into the interior.

Rubbing sleep from his eyes would have been a joke.

After working the past six to seven years as a solo hunter had prepared him for the extra long drives with no copilot . It was just him and the open road most of the time.

That wasn't a big issue for John, but he was ready to leave the vast wilderness of northern Michigan behind.

Wendigos were nothing new to John. He could tell you the history and mythology that lead to their horrific beginnings, where they were usually located, their talents, and how to off one. Hell, he had each fucking detail written down in his damn journal. The only thing that ever changed was the timing of its particular hunting season, or it's location.

This time, the location had royally screwed John.

* * *

After several missing persons cases, all of which were drawn up to ill informed hikers or bear attacks, John thought it necessary to visit. Only being a handful of hours away, the drive was short.

The case as an entirety, had been short. Drawing up the conclusion of the wendigo attacks had been fairly simple.

Scanning through an array of newspaper clippings and barely there articles spanning from present day back to 1938 gave way to a timeline in which the creature stuck to. Every nineteen to twenty-two years it reared its ugly mug to stock up for hibernation, taking three to five individuals along for the ride. The families of the victims provided little to no information obtaining to the hunt. The best they could give was a general area in which the person had been heading.

After glancing over several cases, circling and crossing out different sections of the Porcupine Mountains, John had narrowed the wendigos whereabouts to a rarely used trail deep in the forest. Within a seven mile radius arose two caves, one of which he was fairly certain was the monsters den. The northern cave was housed farther from what seemed to be the general destination off the missing persons, where the western cave was closer to the zone where the people seemed to be disappearing from.

Pulling the truck off to the side of a backwoods road John stuck it in park and dug through the center counsel. Rummaging through a multitude of false ID's, badges, and licenses, he came up with the permits 'allowing' him to be roaming the mountain, should he run into a ranger. Ripping down the zipper of the duffle, he stuffed in the permit and unloaded himself from the car. He went through a mental check list of all needed to make the expedition. Checking once, then twice in assurance, John made sure had had the flare guns. Without them, he was better off dead.

It was late morning by the time he finally started his trek off towards the western cave. In late July, the flies and mosquitoes were floating in steamy packs through the humid air of the mountains. The week seemed to be hitting record highs for this time of year. He was barely into the hunt and already had pools of sweat gathering from the nape of his neck to the small of his back. Sighing in disgust, John kept on his way. He'd been through worse in Vietnam.

A little sweat doesn't break a Winchester.

Three and a half hours later, John was finally nearing the western cave. He reached around his back and flung the duffle onto a nearby boulder. After opening it, he rifled through the contents until he pulled out the two flare guns, and a shotgun. Checking over the shotgun to make sure the safety was on, and the bullets were stocked, John carefully approached the mouth of the cave. He could faintly here moaning from the cave, clearly coming from a human.

As he quietly strode through the entrance, each foot step starting at the heel of his boot and ending at the toe of his boot, he realized something wasn't right. As he disappeared deeper into the cave, a faint glow could be made out the farther he went. As he rounded a bend to the right, John realized he had no damn clue what he'd just gotten himself into.

Inside the cave didn't live a wendigo.

His stomach dropped as he realized he was in the completely wrong location. The thought of having to trek to the northern cave was long gone when he realized that there were at least half-a-dozen people in the cave.

It wasn't even a fucking _bear._

A foursome of small tents were arranged in a half circle around a small fire that had been built. The encampment looked as if it had been set up for days, when he finally looked upon the people.

Through all of his years, John had seen some shit. Not just the monster sort of horrors that make your skin crawl. He'd had the pleasure of receiving motel rooms that were still in use, usually by the hooker from the corner of main street and the mayor's wife- who was happily married- for another forty-five minutes.

Around the fire, lying on a mass of pillows and blankets, were six twenty-something year old college kids in what appeared to be an orgy for all intents and purposes. As he gave a quick glance around the cave, John saw it was also strewn with cigarette butts, empty bear bottles, and still smoking blunts. He felt like he was back in the seventies. He couldn't tell where one body ended and the next started.

Backing up as quietly as possible, John wasn't able to make his escape without being noticed.

"Hey man," one of the kids called. John's gaze snapped to his face, which was situated between a busty brunette's thighs. He had scraggly blond hair sticking to the girls thighs, and bloodshot eyes.

"Do ya wanna stay a while? Plenty 'a room. Don't they say seven's a lucky number, guys?" The stoned boy said, glancing amongst his groupies. The others mumbled in eager agreement, whatever high they had making them easily agree to any decision. If the scraggly blond boy said drink bleach, they'd down a whole gallon just to go with the flow.

Speechless, John just kept on stepping backwards until he was out of the cave. He didn't stop until he stood over his duffle he had left on the boulder outside, starring at it in shock from his latest encounter. It took a lot to knock John off his block, but this had done it.

Shaking his head to snap himself back into reality, he looked at his watch for a time confirmation.

It was three in the afternoon.

There was no way to make it to the northern cave, kill the wendigo, _and_ get back to the truck before sun down. He sure as _hell_ wasn't going to leave himself out as easy bait. Wiping a hand down his face in agitation, he realized he'd just wrecked the simplest of hunts.

" _Fuck_."

* * *

By eleven that evening, John had finally rolled into an old-fashioned wooden-paneled bar.

Scrolling, through his phone, he'd quickly texted a local hunter the coordinates and backstory about the hunt. (Leaving out his miss steps he'd taken to the western cavern and its inhabitants.) He was leaving with what little dignity he could scrounge from the Porkies.

Walking up the steps of the bar, the sounds of glasses clanking, billiard balls busting, and music booming could be heard as John pushed through the old rusted doors.

As soon as he had two feet within the bar, all sounds stopped. Glasses were held in mid air, the music turned to a barely audible sound. Over the last year or two, John had finally become accustomed to his now famous status.

In early 2004, John had finally gone toe-to-toe with the yellow eyed demon, Azazel. After months of tracking acquaintances of the demon, and keeping track of crop and electrical failures, he'd finally met the son of a bitch in a crooked town on the northern border of Wyoming.

With the infamous Colt in hand, and few words exchanged, John had pulled the trigger. Things played out as John could only imagine; he watched as the bullet tore its way through the meat suit until it inevitably reached the heart, ending the demons long rain of terror.

Strolling past the suddenly quiet crowd, John took a heavy seat on the nearest bar stool. With a sigh, John rolled his shoulders back and locked eyes with the bartender, "A bottle of bourbon. Jim if you've got it," John ordered.

With fumbling hands, the bartender bumbled his way through the bar trying to get the order out as quickly as possible for _the_ John Winchester.

A loud thump alerted John to the man who'd seated himself in the next seat. Looking out of the corner of his eye, John recognized the man as Jack Roberts, a low-ball hunter. Jack was a man more up on the gossip than the hunt.

"Where you headin' Johnny?" Jack said, loudly rolling a worn tooth pick between his yellowed teeth.

"South. Got a poltergeist down in Jacksonville," John muttered, eyeing the bottle of Jim coming his way.

The bartender set down a tumbler and bottle. John already knew it was on the house. He rarely paid a penny out of pocket around other hunters. Nodding in thanks, John ripped the top off the bottle, dumping the amber liquid til it hit the rim. Picking the glass up, he took a deep swallow, drinking the liquor like a fresh glass of lemonade.

"Saw your boy down in Nashville. He's askin' if I've seen ya lately," Jack blurted, bushy eyebrows raised, waiting for John's response. He was like a dog waiting for a treat; on edge, waiting for the info to spill from one hand into the others mouth.

Taking a deep breath, John let the scent of the bourbon waft through his nostrils, he barked, "And you haven't seen me lately," his eyes glared into the red neck's eyes, "isn't that right Jack?"

Grinning with what few teeth he still had on full display, Jack nodded his head up and down in a dopey manner, "Johnny you say? I ain't seen hide nor hair a him in _years_. _Years."_

* * *

 **A/N: Sorry for such a long wait guys! I've been writing bits and pieces, trying to get everything put together. I'm happy to finally be able to get something out to you guys this week. Please read and review, tell me your thoughts! The next chapter will finally make it to present time, from Dean's point of view no less! Thanks for all the love you guys have been giving me, it's more than I can even imagine receiving or deserve.** **Have a good week!**

 **Indigo**


	4. Chapter 4

Present day

 _Oklahoma City, Oklahoma_

What nobody had ever told Dean, was that a salt-and-burn was never simple. _Never._

You had to scrounge through old news clippings looking for the right facts, make sure you didn't totally blow your cover talking to locals, _and_ that most spirits usually popped up right before they flamed out.

 _Especially_ that they always popped up- like Angelina Simmons, per the moment-out of the damn thin air, and gave you a nice big lift off that hurt a hell of a lot when you finally landed.

With a groan, Dean pulled his body upright. After a few too many shots, and a romp with "The Terrible Twosome", Tina and Tracy- who were pretty damn twisty- the multitude of activities he'd participated in just didn't mix well together. Blinking a couple of times, Dean rolled over and pushed himself onto his feet.

All he had to do was get from point A (also known as where he was standing) to point B (which meant getting past not so angelic Angie) light some matches, and throw them onto the gasoline-saturated, heavily salted bones.

Easy my _ass._

Reaching into the waistband of his jeans, he pulled out his old sawed of shotgun. He had no need for new and shiny objects. Old and trusty worked just fine.

Cleaning Angie-not-so-Jolie out of the way with a few rock-salt rounds, Dean dug through his coat pockets for the matchbook. Grasping a hefty amount in hand, he ripped them down the coarse paper, the friction illuminating the air with sparks of flames. With a flick of the wrist, the matches landed over the broken bones, lighting up the corpse in a roaring fire.

Rubbing the middle of his back, Dean surveyed his handiwork. Mentally ticking of the hunt, he looked at the piles of unearthed dirt with a grimace.

Working solo really had its down falls.

* * *

After a grueling hour of filling in the grave, Dean had finally completed the task. With legs that dragged as if there was an additional weight around his ankles, Dean finally made his way back to the Impala.

If there was anything that had stayed consistent in his life, it was Baby. The smooth metal exterior shone from the moonlight, the chrome finishes giving a special twinkle in the night light. After throwing the shovel and other items into the trunk, Dean slid in behind the wheel of the car. He could practically feel her hugging him back as the leather molded to his body. Putting the car in drive, the roar of the engine was equivalent to the sound of tweeting birds on a warm summers morning.

This was home.

After Sam and John had left Dean in the dust, it was like a kick to the crotch. You could sympathize when it happened to someone else, but it was a whole 'nother realm of agony when it hit you.

Not knowing anything but following orders his entire life, he'd picked up the slip of paper and made his way onto the next hunt. The only rule he had broken was calling Sam. Because there was no way that heaven or hell (or John Winchester) could keep him from talking to his brother. The only thing he hadn't counted on was that Sam would be the one to keep the connection broken.

Not a _single_ time did Sam pick up the phone. Not. One. Time.

That was the breaking point. Dean could take the fact that Sam was going to school. He was so damn pigheaded that he knew one way or another his little brother was going to make his dreams reality. He'd just never thought that Sam's dreams didn't include _him_. Having Sam leave him behind in the dark was as bad as mourning for a lost loved one. He still felt the clench in his chest at his name and felt the sting of tears in the back of his eyes.

After finding no middle ground with Sam, Dean tried to at least look at the situation in some good light. He still had his dad around, he still had _some_ family. He just needed to reconnect with John quickly.

Wrong.

The last time Dean had seen John face-to-face was four and a half to five years ago, after John had killed the yellow eyed demon.

He'd received a short voicemail telling him to meet up in a hole-in-the-wall diner in Portland, Oregon. The weather had been dreary by the time Dean had arrived for a late breakfast at the diner. Already situated in the booth was John Winchester himself. Little had changed about the man; maybe his face was adorned with a couple more creases or bruises, but it was the look in his eyes that still held the same military man. Dean sat himself on the other bench of the booth when John didn't rise to greet him. John gave a monologue that lasted fifteen minutes at most before leaving. The only two main points Dean was able to make out were,"The demons dead. I caught up to him around Wyoming and shot the son of a bitch straight through his twisted piece of shit for a heart," and "I think it'd be best we go our separate ways now. God knows you're too damn old to be holding onto the tail of my shirt every place I go. More cases are covered if I go my own way and you find something to do on your own. I don't have room for hungover mistakes."

That was the last time Dean had talked to John. Any attempt at calling his phone ended with dial tones and voice mails.

It was, in fact, the final nail in the coffin. There was no place for him in either John or Sam's lives if he wasn't wanted, which they had made painstakingly clear. He was just an extra bed to pay for or a waste of time.

In most ways, Dean had then left the world of hunting. He would grab odd jobs at auto shops, and hustle pool when all that was left was spare change. He kept an eye out for anything sounding suspicious, or of supernatural quality, in case he needed to make a pit stop.

Dean kept away from the hunter friendly bars, the sympathetic gazes the others cast towards him enough to make his stomach revolt.

The only 'relations' he took part in lasted for an evening, occasionally into the morning at most.

He wasn't attaching his strings anywhere in hopes of finding a home, then having it pulled out from beneath him.

He was better off alone.

* * *

By ten o'clock the next day, Dean was ready to head out of town.

He had just one last stop at his P.O. box before he hit the road.

Stepping into the well air conditioned room, he made his way over, shoving his key into the appropriate slot. After a couple of twists and tugs, the box was open. Grabbing the thin stack of mail, he rifled through it until he pulled out an envelope of finer quality than the rest. Shoving the rest under his arm so he had both hands to work with, Dean starred at the letter addressed to him with a furrowed brow. The letter lacked the I.D. of whoever had sent it.

With a shrug of his shoulders, and a mumbled "Maybe it's my lucky day", Dean tore open the envelope. Maybe it was some hot vacation or misplaced money. Instead, he pulled out what many would find to be a beautiful invitation.

Dean could feel the blood drain from his face, and his stomach begin to flop like a fish out of water.

In neat cursive, surrounded by perfect swirls of decoration, the card read:

 _Mr. and Mrs. Moore request the honor of your presence at the marriage of their daughter_

 _Jessica Lee Moore_

 _and_

 _Samuel Winchester_

With a slam, Dean closed the box. As soon as it had clicked shut, he began to smash the top of his head on the hard shell of the box a number of times.

Taking a deep breath, he let his forehead rest on the cool metal in silence.

Tilting his head towards the ceiling, as if he were addressing God himself, he moaned, "Is this your idea of luck? 'Cuz _man_ does your timing suck. Stupid damn luck."

* * *

 **A/N: I was happy to finally be able to squeeze out another chapter this week since my timing usually is rather terrible and unpredictable. So here is something to read as you finally reach the weekend! Little bit of a cliffy, but more to come! Hoorah!**

 **On a side note, thank you for the reviews, follows, favorites, etc. I thought that I would post a story that maybe, _maybe_ , would get a teeny tiny amount of attention. Then I was shocked to see the amount of followers sky rocket past my goal! So thank you to the moon and the stars for reading my little story out of all of the others. I truly appreciate it.**

 **As you leave, don't forget to write a quick review! I love any sort of feedback, because I really do try to acknowledge what you guys think.**

 **Thanks and have a lovely weekend y'all!**

 **Love, Indigo**


	5. Chapter 5

_Chapter 5: Krispy Kreme's and Old Dreams_

"I'll take three dozen Krispy Kreme's to go," Dean rattled off to the doughy bread boy behind the bakery counter, picking up a couple of beef jerky sticks along the way. Well over a day spent behind the wheel, and probably what measured out to be a gallon of coffee running through his system, and Dean had made it to Palo Alto.

Once the shock over the invitation had worn off **-** though it really hadn't, because Sammy was getting _married-_ Dean had rifled through the other contents that had came inside the envelope. Following the wedding invite were a list of dates for a whole bunch of occasions, like the Bachelor Party and a wedding shower _brunch_. He'd never been invited to a brunch a day in his life, and figured putting two meals into one meant double the food, therefore the event _had_ to at least go okay.

Rushing to Palo Alto wouldn't have been his first thought, since he still was trying to wrap his mind around everything. The problem was, he only checked his P.O. box when it was convenient, which meant the envelope had been in there for a bit. Which also meant that the date for the brunch was only _two_ days away. Being in Oklahoma City and all, it made for a long, nail biting trip to California.

Seeing Sam again for the first time in ten years, truthfully, made him sick to the darkest pit of his stomach. He'd gone over every single detail, from whether he should say 'hey', 'hi', or 'hello', to what lie he would be telling his future sister-in-law- _a fucking s_ _ister-_ and her family about his job. And what if things went terribly wrong, and he was asked to return the rest of the invitations? He didn't think he could bear being that close to Sam for what felt like the first time in forever, and having it ripped away. If the first time didn't do him in, surely the second time would.

But, there were always the positives. Somehow they'd kick it off right where they had left off, two brothers glued at the hip. Dean would get along great with Jessica and her family, and he would be able to fit the dusty old puzzle piece of his life back in with somebody else's. Some where along the way, maybe even Dad would get his head out of his ass and _finally_ see the wrongs he had made, and actually _learn_ a couple of things that a father was supposed to be and do. Sure, it all sounded as cheesy as that spray can shit. But it was that little glimmer of hope he had locked away in the depths of his mind, that had kept him going all these years. He had come to realize, his life wasn't worth much if there wasn't a single person to share it with. And he wasn't going to pass up this opportunity to fix this royally fucked up mess.

Grabbing the fresh donuts from the counter, a polite nod to the dough boy, and Dean was on his way out the door. It was now or never, and he sure as hell wasn't waiting for never to happen.

He slid onto the sleek interior of the Impala, put the donuts aside, and started on the final stretch towards Sam. Looking at the dozens of donuts, then back to the street, all Dean could imagine was Sam occupying the seat beside him. His head cricked to the side at a painful angle, while a light snore departed from his lips in slumber. Or perhaps his eyes scanning over the endless lines of a novel, a flashlight held between his shoulder and jaw to brighten the pages. It had been years since anyone had sat himself in the passenger seat. There wasn't anyone to yell "shotgun shuts his cakehole" to over the roaring of Zeppelin, nobody to tell his terrible jokes to, or ruffle their feathers with his explicit stories. It had been years since he had felt the crinkle of a smile, a _real_ smile, stretch across his face. Even with a woman in his bed, or in a full bar, he was forever lonely.

Without his family, Dean felt little purpose. Among hunters from coast to coast, Dean felt inferior, that his small contributions were the minnows among the great white's.

For the first time in 10 years, Dean felt purpose again.

* * *

Though the suit was obviously nothing of great expense, Dean knew being the lone member to represent the Winchester side, that he had to step up his game. Usually it was retired to the trunk of Baby, only of use for the research leading up to a hunt. For once, the cheap black suit had finally brought more purpose.

Even with the suit on, Dean strode through the sea side country club with a facade of arrogance radiating outwards. To be honest, he was scared shitless. This was by far the last place he would picture himself, next to out on the golf course itself. He could feel his skin itching to throw on a flannel and some worn jeans. He'd rather be tuning the Impala, grease staining his fingertips, an open beer bottle within his reach. Making his way to the private banquet hall in the west wing of the building, Dean took a deep breath as he heard the laughter and conversation that faintly leaked from the room, standing just outside the doorway.

"Now or never, hot-shot. Time to get a taste of that apple pie." Dean muttered, a useless pep, but it was better than nothing.

As soon as his feet hit the floor within the room, he was immediately struck by the arrangement of people within. He couldn't spot a woman without jewels lining her fingers, wrists, ears, or neck. They were pieced together like those of the woman lining the thick paged, heavy magazines. They were all women of money, their looks and wording portraying so. The men all had a dazzling class ring from the most renowned colleges wrapped around there callus-less fingers, tailored suits fit to there bodies, and forever ticking Rolex's latched to their wrists.

Then there was Dean, standing with his Krispy Kreme's and dressed in a suit the cost of a plate to eat at a place like this. He could feel their questioning eyes molesting him.

Trying to find his wits, Dean walked towards the buffet, hoping to squeeze into the rich atmosphere of the brunch setting. As he set the boxes of donuts down among fruit that sure as _hell_ wasn't your average produce, a voice rang from behind his shoulder.

"Dean?"

* * *

 **A/N:**

 **Sorry for the long wait guys, I just got the time to put my fingers to the keyboard to pump this out. I'm expecting to have the next chapter out within the next week or two (hopefully). Any guesses on who's behind Dean? Please review, follow, favorite, etc., I'd greatly appreciate it. Unless this story is really a piece of shit, then let me know. Don't be the person who doesn't tell their friend they have lettuce stuck in their teeth;) I adore you all.**

 **Sending my love,**

 **Indigo**


	6. Chapter 6

_Chapter 6: The "Family Business"_

Dean's eyebrows furrowed in confusion at the voice. Turning away from the safety of the Krisy Kremes, he met the gaze of a soft, happy pair of eyes and a relaxed, though nervous, smile. With a raised eyebrow, they spoke.

"It's so nice to finally meet you; I'm Jessica, but you can just call me Jess," she said. I don't know what I had expected from Sam, but it was totally _not_ this. Jess was a perfect ten-outta-ten; she had a mass of blonde ringlets that shifted at every movement, and the body of a centerfold from-what he could make out from her blush colored dress. Sammy had certainly scored big in the looks department, and she probably had some brains to go along with them. Sam had never been much for dumb blondes, or any dumb chicks for that matter. As soon as the obnoxious laugh and hair twirling started, Sam would already be gone.

With a genuine smile, Dean shook her outstretched hand and shook it, "Nice to meet you, too. I've gotta say, I'm surprised Sammy could land a knock out like you though. What'd he have to pull to get that ring round your finger?"

With a light laugh, she replied, "To be honest, _I'm_ the lucky one. I can see it's in the family, that you're all so good looking," Jess winked, "but Sam didn't have to pull any tricks. He's such a hard worker, and he's so devoted to his friends and family." As she finished her sentence, her face wrinkled with worry. She looked down at her manicured nails and began to pick at the cuticles.

"I know you two haven't seen each other in a _really_ long time, and, well, I just felt that Sam would regret it if you weren't here for all of this," she mumbled, a deep red beginning to mottle her cheeks.

Dean's face, however, was the exact opposite. He felt the blood draining rapidly from his face, his features melting away from their happy positioning.

"I found a P.O. box address a while ago-your P.O. box address-when he was getting rid of some things, and I thought it would be best to save it for something like this," Jess finished, the edges of her nails beginning to brighten from her scratching and digging.

"So, what you're telling me, is that Sam has _abso-fucking-lutely no clue_ that I showed up for _his_ wedding shit? That this is gonna be the best surprise of his _life_? Let me tell you something Jess; _I_ have tried getting in touch with Sam. I've called him, I've sent him mail, hell, I even tried dropping in once-he didn't show. When he left, he meant it. When he told Dad he didn't want to see either of us, that he wanted _no_ part of the family business. He made it crystal clear he didn't want to devote his life to something like hun- to something that he couldn't give two shits about. That he didn't want to turn into someone _exactly_ like our dad. And honey, the kid I knew had quite a temper. And I'm guessing he's still got it, and things aren't gonna be really pretty when he finds me here," Dean said, his voice tight with restrained anger.

When Dean was finally through, he took a deep breath to steady himself. Sure, he knew things wouldn't be lolly pops and frickin' candy canes, but he didn't know that he was walking into an inevitable shit show. He wiped his hand down his face, rubbing his throbbing temples.

Jess's head lifted. Her face contorted into a look of confusion. "Why wouldn't he want to be-"

Dean tuned out the rest of what Jess was saying as he made eye contact with a tall man with chocolate colored hair and _those_ eyes. The same ones that looked up at him when he needed his shoes tied at the age of four, the same ones that always begged him to buy an extra bag of skittles at the gas station when they had spare cash.

Sammy strode through the room, quickly making his way to his bride-to-be's side. No longer the lanky teenager who needed his big brother by his side, Sammy was taller than him and had filled out. And maybe- _maybe-_ just as good-looking as himself.

With his jaw locked, Sam was able to bark out the few words, "How'd you know about any of this? Why are you here?"

Jess opened her jaw to fess up, but before a sound could come out, Dean responded. "It's nice to see you, too, Sam. Your girl here decided to send me a list of dates for your wedding and all that jazz. I figured you needed someone to represent our side of the family here and thought I'd stop in," Dean's face suddenly turned more serious, " I mean, c'mon Sammy. You're getting _married,_ like monkey suits and stuffing cake in each others faces. I couldn't-wouldn't-miss it for the world."

Sam's face began to morph into the same one when he'd broken a toy, or told the wrong story to the CPS lady making her rounds. He was hiding something. I looked over to Jess, who looked somehow even more confused.

"Sam, what does he mean? I mean, your dad and-"

"There seem to be a problem here?" John Winchester interrupted, his voice a deep rumble. Dad and Sam exchanged looks, communicating solely between the two. It was obvious that there were, for some unknown reason, no issues between the two. The hatchet was obviously buried.

"What the _hell_ is going on? And don't leave out all the itty fucking bitty details, cause this shit ain't natural" Dean yelled.

* * *

 **a/n:**

 **Happy I was able to get this out to you guys! We've got the whole gang back together, and shit is gonna fly! Thanks for reading if you happen to be doing so, and please review, favorite, follow, etc. Tell me what you think is going on, what you don't like, what you do, etc., as long as you aren't too spicy about it;). Have a great week guys, and thanks for your time!**

 **-Indigo :)**


	7. Chapter 7

_Chapter 7: In the Dark_

The snapping of the heels from the dress shoes worn upon the three Winchesters' feet echoed angrily against the walls of the hall leading to the outdoor patio of the country club. Dean strode ahead of Sam and John, knowing his temper wasn't going to last long. He lead them at a quick pace, ready to see _all_ the cards, not just the ones Sam and John wanted him to see.

Wrenching open what were probably very expensive, hand-crafted french doors with handles that shone with a bright chrome polish, Dean strode out the doors. The patio, momentarily empty, had a spectacular view over the golf course. The fairways rolled and curved smoothly along the hills of the coast, a glimpse of the Pacific seen in close proximity. The course as a whole looked as if it was brand new; not a chunk was taken too deeply from an iron shot, and the greens were without the divots from a ball gouging its surface. Tropically colored flowers on vines that looked from the most gorgeous of jungles wrapped around the trees and bushes, spreading along the wooden structure of the pergola. The patio floor consisted of large, marbled tiles of rich grays and deep blues. They were precisely organized on the floor, and not a blemish could be seen on the marbled tiles positioned in the thick and dry cement. A wide array of wrought iron tables and chairs were spread out on the patio for their patrons to sip their expensive sangria and to munch on their pate and caviar.

Dean could feel his blood boil waiting for them to catch up. All he really wanted to do was pick up one of the chairs and hit the ground again, and again, and again, until his anger would finally diminish.

Caught in thought, he heard the french doors shut as Sam and John stepped out onto the patio. With green eyes blazing, Dean turned to them. Before he had a chance to speak, John had already began with a frown pasted on his face.

"This is the last of places to be throwing a tantrum, Dean. Have a bit of respect for your brother and his _fiancee,_ this isn't just some bar you can crawl in and punch the nearest beer-bellied hillbilly that gives you the evil eye." John rattled off, as if he were scolding a fourteen year old for peeping at the neighbor's daughter.

Dean could feel his temples throbbing with the pressure of blood coursing thickly through his veins. His hands itched so badly to crunch his knuckles into the face of somebody, anybody. Especially his father.

" _Because this is the last of places that I've_ seen _or even talked to you in_ years!" Dean snapped, the throbbing in his head intensifying with his anger, "I've looked for you from San Francisco to Portland _fucking_ Maine!" He roared. "I've asked _every_ guy at _every_ roadhouse if they've seen you, or talked to you, and I don't get _jack shit_ from _anyone_! And I show up here, and all of a sudden you act like you raised a couple of nice boys inside some picket white fence. Wait, no, that ain't right either," Dean said with a chuckle that didn't hold a hint of hilarity, "because you sure as _hell_ didn't raise us. We grew up in a car, or in the shittiest, dankest, cheapest motel you could find, and left us while you went out on a hunt. Maybe you even left a little money for food, but that _sure as shit_ wasn't the first thing on your mind. You maybe taught us how to gamble, or to not get a girl knocked up 'cause we sure can't stay in one spot, but you didn't raise us, especially not to be _nice_."

Slowly a dark red had begun to spread through John's face with each of Dean's words.

With his eyes still trained on John, Dean continued. "But what I really find _hilarious,_ is the kid that you kicked out, invited you to all his wedding shit," Dean said, glancing between both of the dark haired men, the fire in his eyes somehow darkening, "and that nobody thought that, you know, _I_ might want to see my dad, or come to my kid brothers' wedding. You guys know, the one _I_ raised. So, somebody better flip the fucking switch on and get me out of the dark, or I'll flip the fuck out at the swanky little country club."

Scrubbing his hands over his face angrily, John gave out a sigh.

"The thing is Dean, you've never been on your own. You always had Sammy with you since you watched out for him, and when he was gone, you were there in every last footstep I had taken. You never found something you were good at." John began. Dean could feel the blow to his gut, but wasn't going to give the satisfaction that his dad still held such influence over his confidence. "So after I killed that bastard demon, I figured I needed to cut the strings loose. Let you go hunt solo, try and make something of yourself."

"Then why couldn't you have answered the _God damn phone and told me to get the fuck out of the way?_ I sure would have listened, _damn it_ , when have I _not_ listened to every last word that came outta your mouth?" With each word the throbbing intensified. "I just wanted to know if you were dead, alive, MIA, _anything_ would have worked for me. And not _one_ person could tell me where you were, what your last hunt had been. Nothing."

As those last words left his mouth, Dean felt something give way in his head. It was something he had never thought or even _dreamed_ John might do, but anything was possible.

"You're not hunting anymore, are you?" Dean said quietly, gauging both John and Sam's reactions. The muscles running along John's jawline tightened, and Sam stared down at his feet.

"And lemme guess one more thing; you settled down 'round Sammy, fixed things up?" Dean said, still keeping his eyes on both of them. All John could reply with was a curt nod.

For the first time in years, Dean could feel the burning of tears behind his eyes. He had hunted all these years, because that was what had been expected of him. Because that was what he was _supposed_ to care about. It was the "family business" after all. He shook his head with a cruel smile. Everyone had always been right. He had a pretty face, but where were his brains? The boy couldn't even high school, what use was he anyway? His head still throbbed viciously, as if his brain was trying to bust out of his head.

Biting the inside of his mouth, he looked back up at them, ready to finish this. "Before I get out of here, let's make this clear since I'm obviously a couple screws too short to understand where I'm not wanted," Dean choked out, though it was heard stronger to Sam and John. He then met John's gaze and held it with ironclad strength, "And I swear to God, that you better take care of yourself, and you better not shoot things straight to hell with Sam again, or else you'll just have to deal with me again. So let's make it easier on ourselves and not have that happen, am I right?" Dean cracked, even though not a single one of them found it funny.

He could tell Sam looked like he had a million and one things to say, but he didn't think he could take a scolding from his baby brother after the way the day had turned. John looked like he was trying to chew and swallow a handful of nails.

With a lump in his throat, Dean forced out a sigh, "So that's it, right? All the cards on the table? I'm outta the dark?"

John yet again scrubbed his face with his hands, going up to pull at his dark hair, now laced with hints of grey. Sam's face was twisted up like he hadn't shit in a week, and he began to pick at the cuff of his sleeve. They were both signs of irritation and stress, and also as close as someone like John Winchester ever came to being nervous. His forehead creasing in confusion, and eyebrows furrowing together, Dean continued to look between his family.

It was John who finally cleared his throat, and with a shake of his head said, "Not all the cards are on the table, Dean. I know I should've told you this already, but it never seems like the right time."

When John didn't continue, Dean looked at him with confusion. "What'd you do, slip one past the goalie?" he joked.

Silence.

Dean felt his face drain, the color fading but the throbbing in his head once again intensify. "You've gotta be kidding me, right?" Dean egged his father on, trying to get some semblance of a correct answer.

"If you come back in, you'll get to meet him," Sam interrupted, having been silent, "his, uh, his name is Adam."

* * *

 **A/N:**

 **I know a couple of you probably wanna toss a couple of punches my way for taking so long, which is understandable. I have been all over the place, and just got back in the swing of things after a much needed vacation to the Caribbean. Surprise, surprise, Adam is here, and yes sir, John & Sam have themselves in a bit of a tough spot. Anybody got any ideas about what's coming next, etc? Let me know what you think about this chapter and any of the others, I love hearing feedback from y'all. Hope everyone is having a lovely April, and happy very belated Easter! Send me any questions or recommendations if you have any!**

 **All my love,**

 **Indigo**


	8. Chapter 8

_Chapter 8: One and One and One is Three_

There wasn't a hell of a lot of information from his time at school that Dean had committed to his memory. There were the basics of course, like reading and writing that had stuck with him. He may not have been or be some brainiac, but not all of the screws were loose in his grapefruit. And yes, being able to successfully sing one hundred bottles of beer on the wall was one of those basic skills he awarded to his imprisonment within the boundaries of the public school systems math classes, and maybe a little bit from John Winchester.

One of the stupidest tid-bits that had slipped through his ears and jammed its way into an open crevice of his brain was from his freshman English teacher, Ms. Rabbit. He'd expected to have an old, bony woman teaching the class that resembled Bugs Bunny, answering the classroom door with a, "What's up, Doc?" Man had he been wrong though. The only kind of rabbit he could relate her to was a bunny. And not the cute kind like Thumper from _Bambi_ (not that Dean had ever seen the movie anyway). Ms. Rabbit was more like a playboy bunny; she was every teenage boys fantasy come to life, right down to the glasses that slid down the bridge of her nose and the way her clothing fit so well in all of the right places. Whenever she snapped her ruler on the desk, every person with a dick in the class began to sweat.

Just because she was a looker didn't mean that she didn't rightfully deserve her position as a teacher. Sure, there were plenty of teachers that weren't fit to so much as step into a classroom or sit their ass behind a desk, but Ms. Rabbit was not one of them. Most people couldn't help the stereotype that rolled to the forefront of their brains- especially the ones below the waist- rather than who she was as a person. She was by far one of Dean's favorite teachers because of her attitude. She didn't take shit from any kid, no matter if they were the mayor's kid or were big and strong enough to beat the ever living shit out of her where she stood. She wasn't spineless, and was always able to force-feed a healthy dose of English crap down your throat like a big damn spoon of slimy canned green beans; whether you liked it or not, you were going to take what she was dealing.

Of course, not all food stays with you forever. Eventually, you shit it out, unless some of it sticks around as a nice little side of fat. I guess I got a nice slice of apple pie shoved down my gullet when she was teaching at one point or another. That bit of fat that seemed to stick around that hadn't seemed to burn off in all of these years was about stories. Typically in stories such as fairy tales, numbers of three and seven were commonly used. Kind of like how that dark haired chick was followed around by seven midgets, and how that blondie in the pink dress had those three irritating fairies waving their stupid damn sticks around.

So, how the fuck is any of this relative anyway? Dean sure didn't mind thinking back on Ms. Rabbit, but the information he had learned from her wasn't thought on often. Especially since Dean knew he didn't live in no fucking fairy tale. Sure, he rode his black beauty everywhere, but that also was supposed to mean he was as rich as Bill Gates, which sure wasn't true. But at this moment, what had once been stuck within his mind came yelling at him, making his ears ring and his temples throb. This was all just a big ol' game for God, and every story needed the right numbers, right? So why not throw another kid into this fucked up situation, if not to only make the numbers look nice at three? Because that's exactly what seemed to have happened in Dean's case.

In the years spent by himself, Dean liked to think he had matured more than he would have if he had had an actual person to converse with. Singing along to Bob Seger on the rolling stretches of pavement across America seemed to have aged him somehow, with no back up singer or somebody to duo with.

After all of the appropriate individuals had been pulled off to the side, John and Sam went on a lengthy spiel about how dear old Kate and Adam Milligan (present in said room) had made their way into the danger zone of the Winchester's life. After Sam had left Dean for college, and John had defeated the yellow eyed bastard, Adam had made contact with John. He could see the timidity shining in everybody's eyes, waiting for one of his blood vessels to burst, maybe even some attention drawing heart attack (they'd probably blame it on a ghost any way) as they explained the details to him. But no, he remained cool as a damn cucumber as those yuppy dickwads would say.

A nice little visit to Wisconsin lead John to throw in the towel on hunting, calling in his retirement. Decided to patch things up nicely with Sam, even put a nice damn rock on Kate Milligan-now-Winchester's left hand. There was an absolutely _lovely_ family portrait including the three and Sam who had flown over for the occasion. Dean found it pretty fucking funny how _his_ invitation must have gotten lost in the post. He'd known the government was shit, but _jeez_ he didn't know the apocalypse was knocking at the door.

However, Dean couldn't find it in himself to genuinely hate Adam. The kid was bright and witty, maybe not a full on Winchester, but he was family. And he knew from experience what it felt like to be rejected by your blood. Plus, the kid was going to be a doctor one day, and sooner or later Dean would be knockin at his door asking him to fix up something that his own "medical training" wouldn't cover.

After all was said and done, everybody continued to stare at Dean with wide eyes. It wasn't quite fear lighting them, but more of a weary film that glazed their eyes since they expected Dean to burst into a fit of rage. And hell yeah, all 6"1 of him was about to burst from the abandonment and anger, but he was a different person. Sure, he was still trying the whole cool cucumber gig, but there was more to it than that. They all had changed, and he had the right to have become a different person over these past ten years, too.

One of those things that Dean had learned was to listen to what wasn't being said. And he was able to hear a _whole_ fucking lot. Standing calmly from the chair he'd been seated in, he made eye contact with John. "If you guys would just give me a minute to take this in," he said with an amount of coolness in his voice that Gandhi would be jealous of. With his best Arnold impression to convince them, he crossed the room, throwing out an, "I'll be back," with a smirk as he left the room.

Dean traced his way carefully back through the halls of the country club to the rented banquet room. Spotting the mass of curls he'd been looking for, he approached Jessica-almost-Winchester. Giving her a light tap on the shoulder, he asked if he could talk to her in private for a moment.

"Of course!" She exclaimed, moving quickly to gather her cup and follow Dean to a deserted table. She reminded him of a puppy in the same way that Sammy used to.

Not leaving any space between, Dean seated himself next to Jess after pulling her chair out for her- because he was a fucking gentleman- before he turned to talk to her.

"So Jess," Dean began, his seriousness as deadly as the approaching topic, "what do you know about the family business?"

* * *

 **A/N:**

 **I know it's a really, _really,_ lame excuse that everybody uses, but I have been busier than a hotdog stand on the fourth of July (stupid pun, I know). I know most of this chapter is fairly boring, but bear with me please. Thank you for all of the reviews and support, I'm always more than happy to hear what you guys honestly have to say. Hope to pop another chapter up soon.**

 **Until then,**

 **Indigo**


	9. Chapter 9

_Chapter 9: Why can't we be friends?_

"So _that's_ why he was always so weird about the salt," Jess chortled, her head thrown back with great amusement. An occasional snort would interrupt her laughter when she was having a particular fit. Her hand would wave through the air with the crystal wine glass occupying her elegant hands, only half full, though she could refill given the ornate decanter that sat on the table rimming with a glistening riesling. The alcohol left a rosy blush high on the cheekbones on her face, thus giving her liveliness an unneeded booster.

Dean couldn't help but find that the longer he spent with Jess, the longer he could see her with Sam. Hell, in any other situation, Dean would have been hitting on her. But there was something (probably that she was his soon to be sister) that made it seem like it would be more like hitting on your cousin. As in creepy and awkward. It probably helped that she was taking the whole "your soon to be hubby used to hunt monsters" pretty damn well. No vomiting, no big denial, just open ears and understanding. Dean was almost positive that Sam's ears would be ringing a bit by the end of the night after a long, private conversation.

"H-he used to say that it was some 'Winchester family tradition', kind of like praying before dinner," she choked out, her laughter once again putting an end to her words. " _No wonder_ I couldn't find any weird religious things relating to it besides _demons_ ," she bellowed, only stopping to whisper the word 'demons', the tipsiness from the wine coating her words.

Dean laughed, actually _laughed_ , for the first time that he could remember in a while. It ripped its way from his lungs, an unfamiliar feeling that his body had to process. His shoulders shook from the sheer force of it, and deep in his belly ached from the intensity. His head was tossed back, his mouth wide open with the music of laughter erupting. It was a refreshing feeling, like your first jump of the year into a crisply cool lake. It was the way that it should have been able to these past ten years. But the past ten years hadn't been like this. It hadn't been full of gorgeous country club outings and bring-a-dish family dinners. The years had been packed with lonely dimly lit bar nights for one and off-brand hot pocket dinners. The constant vibration of the phone in his pocket an endless reminder as he went about trying to find some bit of happiness in the day.

The laughter seemed to melt off of him then like hot wax, bearing whatever lay hidden beneath. He raised the glass of rich bourbon to his lips, swallowing the remaining contents. Hopefully it would be enough to get him through the day for now. Clearing his throat several times, Dean carefully eased himself into what he'd say next.

"Listen Jess, I'm in a little over my head with the job I'm on and I've gotta kick it outta here. Didn't realize how late it'd gotten," he said, waving his watch covered wrist. With a bitter smile, Dean tried to remain composed, "I'm, um, I'm really happy I was able to make it out this way to see you guys, getting to meet you and all," Dean choked out around the stupid damn lump sitting heavily in his throat. "You're real good for Sammy, I can see that, and it's good to know there's still someone around to take care of him. I wish, I mean I _really fucking_ _wish,_ I could be a part of this family like I should be. This is the most normal kind of day I've had in a while. But the shitty end of this deal is that it's too late for that," he chuckled humorlessly. "Not that it's really what they'd have been looking for," Dean muttered to himself, realizing too late how much he'd given away- _too_ much that he'd given away.

Tipsy and edging on drunk, Jess continued to nod her head, not understanding quite the full meaning of his words and demeanor. Too hazy to clearly figure out every emotion that founded the change in conversation. Before her head could even begin to wrap itself around the turn in conversation, or before she could get a word out edgewise, Dean had risen up from his seat. Giving her a peck on the cheek and a tender squeeze to the shoulder, he walked out of the banquet hall with his suit jacket thrown over his should. Most people there would barely be able to tell that he was lacking the usual swagger he held in his strut.

By the time he made it out to the car Dean quickly opened the rear door to toss his jacket into the backseat before sliding in behind the wheel. He scrubbed his hand over his face, pinching the bridge of his nose trying to remain cool. It wasn't five seconds after he had gotten into the car that his phone began ringing.

"Shit," he grumbled, scrambling halfway into the back to grab his suit coat. With fumbling hands, he began digging in. "Stupid fucking suit with all of your fucking hidden pockets," he growled, his half decent mood shot straight out of the window. Finally locating the correct pocket he pulled the phone from the opening, looked at the number, and answered the phone.

" _I'm on my damn way so why don't you cool it,_ " Dean yelled into the phone, immediately hitting the 'end' button and throwing it into the glove box. Throwing his head back, he gave a grunt of frustration to the roof of the car before shifting her gears to hit the road.

"Just you and me for a couple of hours, Baby," Dean said, the corners of his mouth forcing themselves upwards as his hand rubbed the wheel affectionately. Reaching his other hand towards the radio, he turned the music up and settled in for the ride.

 _I'm on the highway to hell_

 _On the highway to hell_

 _Highway to hell_

 _I'm on the highway to hell_

* * *

It took a grand total of nine and a half hours for Dean to make it to the dry heat of Las Vegas. That time of course included filling up the gas tank, grabbing a cup of coffee and a donut, and taking a piss in a germ infested bathroom in the back of a creepy gas station. The sky was illuminated by the twinkling stars that hung so carefully in the sky, the canyons in the distance making it feel like you were in a giant dome.

Bleary eyed and exhausted Dean spun the wheel of the Impala to the right and pulled into the parking lot of the _El Rancho Motel._ The motel was the typical Winchester style. As in, it was dirt cheap and probably as old as the ground it sat on. The Spanish styled exterior was chipped and faded from a lack of care to the place. The cactuses that were supposed to be used as landscaping were overgrown and frightening, their sharp needles pointing out like vicious spikes on top of a barbed wire fence. And what might have been flowers now were fried to a crisp from the intense sun and heat, deteriorating quickly. To add to the lovely appeal that Dean was forced to 'admire', the ground was littered with a vast majority of shattered beer bottles, pornographic calling cards, and cigarette butts. He gave a shudder and didn't even want to think about what was _inside_ of the motel rooms. He might not be the cleanest fella, but even Dean Winchester had some standard of living.

" _Paradise_ ," he sighed with the driest damn sarcasm in the world- or at least Vegas for that matter. This _REALLY_ reminded him of the country club he'd been sitting in less than twelve hours ago, ornate decor, trimmed bushes and all. Pulling into an empty parking spot- which he had a lot to choose from- Dean threw Baby into park, grabbed his phone from the glove box, and began to get out of the car.

With a symphony of groans, cracking joints, and aching muscles, Dean pulled himself from the car into the dry heat of the night. The lights from the city shone spectacularly in the not too far distance.

"I am getting too damn old for this," he rasped, putting both hands to the middle of his back and arching it in an attempt to stretch. Twisting his body from side to side, he made his way around to the trunk, lifting the hatch and snatching his old duffel bag before slamming the lid.

Finally feeling marginally ( _marginally_ ) better, Dean pulled out his phone and scrolled through his texts before he came to the one he'd been looking for.

 _El Rancho Motel, Las Vegas, Room 6._

Squinting at the doors in the heavy darkness, Dean walked from door ten backwards, until he finally stopped before the sixth door. The number 6 was an old rusted out chrome finish on a peeling and scraped brick red door. Beside the room number he found a sticky note attached. Confused, he pulled his phone back from his pocket and shone the light on the note. An additional two sixes were scrawled on it in pen to make the new room number '666'. Rolling his eyes in what most would call a dramatic fashion, Dean gave six (ha ha, very funny) heavy knocks to the door.

A moment later, the poor excuse for a door creaked open, the room pitch black. Glowing maybe two or three feet in front of his face were a large set of gleaming red eyes. As his eyes adjusted to the dark, he could begin to make out the whiteness of her sharp canine teeth. With a sigh, Dean stepped into the room, the hairs on his neck standing on edge. The set of eyes and teeth backed slightly away from him to admit him into the room.

"We've got work to do," she growled, a salacious grin stretched across her face.

* * *

 **A/N:**

 **Because when I say I'm going to update soon you guys are all supposed to know that it means waiting another month or two, of course- NOT. I know, I know, I'm terrible at the whole 'time' aspect of writing regularly for you guys. It didn't help that I had no clue where this story was going, because I wasn't in for some really cheesy apple pie spinoff that everyone is happy in. Because that's absolute bullshit and we all sadly know it (whether we want to admit it or not). The good news is, I have an _actual_ idea of where this is going for once (not like the rest of my life). I wish I could promise quicker updates, but no, things are about to get busy ****for me. I'm still in awe of the support y'all give me on a regular basis, because Lord _knows_ I don't deserve it. You know I love a good review from any of you  & send all of my love plus more than usual for extreme lack of updates. I know this is a kind of fishy weird chapter, but there is more to come, I promise! Hope you are all enjoying the Olympics as much as I am (which is quite a bit ;))**

 **Regards,**

 **Indigo :)**


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